Synthesis of Enantiopure β-Hydroxy-1,3-dioxolanes by Ir-Catalyzed Asymmetric Hydrogenation of α-(1,3-Dioxolane)-ketones

Enantiopure β-hydroxyaldehydes are important building blocks for the production of various bioactive compounds and commercial drugs. This work describes an efficient and practical protocol for the synthesis of enantiopure β-hydroxy-1,3-dioxolanes via asymmetric hydrogenation of protected β-ketoaldehydes catalyzed by Ir/NNP. Both (R)- and (S)-chiral alcohols can be accessed by altering the configuration of NNP, providing the β-hydroxy-1,3-dioxolanes with efficient enantioselectivity (up to >99% ee) and high reactivity (TON of up to 4600). Furthermore, the processes of derivatization and deprotection were successfully executed.